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Syntheses of Unsymmetrical 1,4-Bifunctional Allylboron Reagents via Cu-catalyzed Highly Regio- and Stereoselective 1,4-Protoboration of Dienylboronates and Analysis of the Origin of Chemoselective Aldehyde syn-(Hydroxymethyl)allylation

Shang Gao, Mengzhou Wang, Ming Chen*

*Department of Chemistry and Biochemistry, Auburn University, Auburn, Alabama 36849, United States, Email: mzc0102auburn.edu

S. Gao, M. Wang, M. Chen, Org. Lett., 2018, 20, 7921-7925.

DOI: 10.1021/acs.orglett.8b03483 (free Supporting Information)


Abstract

Cu-catalyzed highly regio- and stereoselective 1,4-protoboration of dienylboronates provides unsymmetrical 1,4-bifunctional allylboron reagents. A subsequent chemoselective allylboration with aldehydes followed by oxidative workup give diol products with high diastereoselectivity.

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Key Words

allylboronates, homoallylic alcohols, 1,3-diols, hydrogen peroxide


ID: J54-Y2018